496-03-7

Basic information

• Product Name: 2-ethyl-3-hydroxyhexanal
• Synonyms: 2-ethyl-3-hydroxyhexanal;BUTYRALDOL;Butylaldol
• CAS NO: 496-03-7
• Molecular Formula: C₈H₁₆O₂
• Molecular Weight: 144.21144
• EINECS: 207-812-6
• Mol File: 496-03-7.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 216.9°Cat760mmHg
• Flash Point: 86.7°C
• Appearance: /
• Density: 0.923g/cm³
• Vapor Pressure: 0.0294mmHg at 25°C
• Refractive Index: 1.435
• PKA: 14.56±0.20(Predicted)
• CAS DataBase Reference: 2-ethyl-3-hydroxyhexanal(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ethyl-3-hydroxyhexanal(496-03-7)
• EPA Substance Registry System: 2-ethyl-3-hydroxyhexanal(496-03-7)

Safety Data

• Hazardous Substances Data: 496-03-7(Hazardous Substances Data)

Usage

Description

2-Ethyl-3-hydroxyhexanal is an organic compound with the chemical formula C8H16O2. It is a colorless liquid with a distinctive aldehyde-like odor. 2-ethyl-3-hydroxyhexanal is characterized by the presence of an aldehyde group (-CHO) at the third carbon and an ethyl group (-CH2CH3) at the second carbon. The hydroxyl group (-OH) is attached to the same carbon as the aldehyde group, making it a hydroxyaldehyde. 2-Ethyl-3-hydroxyhexanal is an important intermediate in the synthesis of various organic compounds and plays a crucial role in various chemical reactions.

Uses

Used in Chemical Synthesis:
2-Ethyl-3-hydroxyhexanal is used as a key intermediate in the preparation of various organic compounds, such as 2-ethyl-2-hexenal, 2-ethylhexanol, 2-ethylhexanal, 2-ethylhexanoic acid, and 2-ethyl-1,3-hexanediol. These compounds find applications in different industries, including pharmaceuticals, fragrances, and flavorings.
Used in Aldol Condensation Reactions:
2-Ethyl-3-hydroxyhexanal is a reagent useful for the Aldol condensation reactions. The Aldol condensation is a fundamental organic reaction that involves the nucleophilic addition of an enolate ion to an aldehyde or ketone, resulting in the formation of a β-hydroxy aldehyde or ketone. This reaction is widely used in organic synthesis to form carbon-carbon bonds and construct complex molecular structures. The presence of the aldehyde group in 2-ethyl-3-hydroxyhexanal makes it a suitable reactant for the Aldol condensation, allowing the formation of new compounds with diverse functional groups and structural features.

Synthesis

2-Ethyl-3-hydroxyhexanal is prepared primarily by aldol condensation of butanal at 30℃ in the presence of an aqueous sodium hydroxide solution and a phase-transfer catalyst; the reaction is stopped by addition of acetic acid.

InChI:InChI=1/C8H16O2/c1-3-5-8(10)7(4-2)6-9/h6-8,10H,3-5H2,1-2H3

Upstream product

• 123-72-8 butyraldehyde 
• 67-64-1 acetone 
• 110-43-0 n-pentyl methyl ketone 
• 107-87-9 2-Pentanone 
• 75-87-6 chloral 
• 536-74-3 phenylacetylene 
• 94-96-2 2-ethyl-1,3-hexane diol 
• 123-19-3 4-heptanone 
• 1066-30-4 chromium(lll) acetate 
• 60-29-7 diethyl ether 
• 92954-34-2 2-allyl-1,3-dicyclohexylisourea 
• 2043-61-0 cyclohexanecarbaldehyde 
• 6728-26-3 (E)-2-Hexenal 
• 109-89-7 diethylamine 

Downstream Products

• 18618-91-2 3-(hydroxymethyl)heptan-4-yl butyrate 
• 10324-64-8 2-Ethylhexen-2-al-2,4-dinitrophenylhydrazon 
• 27122-56-1 2-Ethyl-1-phenyl-hexane-1,3-diol 
• 27122-53-8 5-ethyl-decane-4,6-diol 
• 645-62-5 2-ethylhexenal 
• 123-72-8 butyraldehyde 
• 123-19-3 4-heptanone 

Relevant articles and documents

Highly diastereoselective aldol reactions of 3-Fluorooxindoles promoted by MgBr2?OEt2/iPr2NEt

A highly diastereoselective aldol reaction between 3-fluorooxindoles and aromatic aldehydes has been developed. Commercially available, cheap Lewis acid MgBr2[rad]OEt2 was used to promote the reaction. The reaction has a broad substrate scope with respect to both 3-fluorooxindoles and aromatic aldehydes, giving a series of α-fluoro-β-hydroxyoxindoles in good yields with high diastereoselectivities (63–94 percent yield, up to 99:1 anti/syn).

Aldol Addition of Butyraldehyde over Solid Base Catalysts

Aldol addition of butyraldehyde was investigated on alkaline earth oxides, zirconium oxide, and lanthanum oxide to compare the active site and mechanism with those for aldol addition of acetone.It is found that the active site is the surface O2(1-) and th

Development of an azanoradamantane-type nitroxyl radical catalyst for class-selective oxidation of alcohols

The development of 1,5-dimethyl-9-azanoradamantane N-oxyl (DMN-AZADO; 1,5-dimethyl-Nor-AZADO, 2) as an efficient catalyst for the selective oxidation of primary alcohols in the presence of secondary alcohols is described. The compact and rigid structure of the azanoradamantane nucleus confers potent catalytic ability to DMN-AZADO (2). A variety of hindered primary alcohols such as neopentyl primary alcohols were efficiently oxidized by DMN-AZADO (2) to the corresponding aldehydes, whereas secondary alcohols remained intact. DMN-AZADO (2) also has high catalytic efficiency for one-pot oxidation from primary alcohols to the corresponding carboxylic acids in the presence of secondary alcohols and for oxidative lactonization from diols.

Amino functionalized chitosan as a catalyst for selective solvent-free self-condensation of linear aldehydes

An aminopropyltrimethoxysilane functionalized chitosan was found to be an efficient solid base catalyst for the self-aldol condensation of linear aldehydes under solvent-free conditions. The modified catalyst was characterized using physical techniques, elemental analysis, FT-IR, and TGA. The modified chitosan was evaluated for the aldol condensation of C3-C7 linear aldehydes in which the selective formation was obtained for α,β-unsaturated aldehydes. A decreasing trend in the conversion from propanal to heptanal was observed. Propanal and pentanal were subjected for detail investigations to study the effect of parameters like amount of catalyst and aldehyde, and temperature on the conversion and selectivity. Kinetic performance of the modified chitosan investigated for a representative aldehyde, pentanal showed that the rate was increased with the catalyst amount, pentanal and temperature. The catalyst was reused up to six cycles without significant loss in its activity and selectivity.